Ladyboy Fantasies
A Short Story by Marlene Sexton
Copyright Marlene Sexton 2012
Published by Red Heels Press at Smashwords
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“Honey, do you think...?” Eileen asked her husband, pointing out a tall, beautiful girl in a tight mini-dress. She was really pretty, a little taller than average but still short by western standards. Mike looked to where his wife pointed and cocked his head. Finally, he said, “Yeah, maybe.”
Eileen sat at a small table at a noodle joint in Phuket, Thailand with her husband Mike. They had always wanted to travel to Thailand, though for different reasons. Eileen loved the exotic culture, the delicious food and the natural beauty of the country, but Mike was more interested in the ladyboys. Mike had been interested in transsexuals since Eileen had known him, but she didn't mind.
Eileen was raised Irish-Catholic, but was more than happy to shed the shackles of that life when she met Mike. He was 25 when she met him at the age of 19. Mike owned a motorcycle shop and his own home and looked to be your typical bad boy. He was tall and muscular, his arms covered in elaborate tattoos. His head was shaven but he wore a long scraggly blonde goatee and rarely wore anything that wasn't mostly black.
Eileen, however, discovered that while he looked dangerous, he was actually a loving, caring, intelligent man with a sentimental side. That's what made her fall in love with him. They moved in together only two months after they met and married later that year. Since then, Mike had led Eileen on a wild journey of self-discovery. Though her family mostly disapproved, she had managed mostly to leave behind her repressed childhood and discover a whole new world of adventure she hardly knew existed.
In the four years since they had been married, Mike had introduced her to an entirely new lifestyle. Eileen enjoyed sex of all types and had found she liked women almost as much as she liked men. They often invited other women to their bed and recently had begun experimenting with other men and couples. Eileen enjoyed her newfound liberation, but sharing it with Mike made it even better.
Now, it was Mike's turn to explore his sexuality. Mike was far from gay, but he had a thing for girls with cocks. Whether it was a pretty crossdresser or a feminine transsexual, he loved them all. He didn't make a distinction between regular woman and transgendered women. To him, they were two sides of the same coin. However, to this point in his life, he'd never been with a transgendered woman of any kind. He seemed more interested in satisfying Eileen's curiosities than his own.
So, for their fourth anniversary, Eileen planned a trip to Thailand. It was a dream of hers to visit the country, but Thailand also offered some of the most beautiful transsexual girls in the world. Asian ladyboys were a favorite of Mike's and Eileen wanted him finally to fulfill his fantasies. Eileen couldn't wait to get him laid by one of those sexy t-girls.
“She's cute, no matter what. I'd do her,” Eileen observed.
“I think she's a girl. She's just too damn perfect,” Mike replied. The girl was shapely and had beautiful, full breasts and long legs. Her skin was a dark olive-brown and smooth as silk. She exuded femininity, from her pretty face, to her long legs. Her platinum blonde hair hung loosely to her shoulders. She wore a sequined purple dress that showed lots of her long shapely legs. Nen had on tall black pumps that made her legs look even longer. In short, she was exactly what they were looking for, if she had a cock.
“Well, we've been looking for an hour. Are you gonna make a move or what?” Eileen asked.
“I'm kind of nervous, honestly,” Mike admitted.
“Mike, just go do it. Quit being such a pussy!” Eileen chided, only half joking. Mike stared at his wife and rolled his eyes. Eileen could tell he was excited, but hesitant also. She didn't blame him. She experienced many firsts in the last four years and every time it was nerve wracking. If Mike hadn’t pushed her, she may have never done any of it and that would have been too bad. Finally, he said, “OK, I'll go, I'll go,” and smiled at Eileen.
Mike took a deep breath, stood up and Eileen watched him walk down the crowded street towards the Thai woman. Eileen hoped she was a ladyboy, but wasn't holding out much hope. She agreed with Mike that she was probably a natural woman. She had seen Asian transsexuals that looked that good, but it was too much to hope for. Too bad, she thought to herself, the girl was really hot.
Eileen watched as Mike approached the woman. She turned, a huge smile on her face, and began chatting with him. They talked for a few moments, the woman nodding now and then. Then the girl began pointing in Eileen's direction. Mike looked and then turned back and they talked some more. Several more times, the blonde Thai woman turned and gestured towards Eileen and then back to Mike. Finally, Mike shrugged and began walking back, the girl following him.
Eileen was a bit puzzled, but excited to find out what was going on. As Mike and the girl approached, Mike said, “Eileen, this is Nen. Nen, my wife, Eileen.” Eileen stood, smiled as she took the girl's outstretched hand and said, “Hi, nice to meet you, Nen.”
Nen gently shook Eileen's hand and said, “I glad to meet you, Eileen.” Her voice was small and girlish and her accent was sexy, but not difficult to understand. Up close, she was just as pretty as she seemed from a distance. Eileen was sure Nen was a natural woman. Even her hands were small and delicate. No Adam's apple, either. Damn! Maybe Mike would let her spend a couple of hours with Nen instead, Eileen thought, but remembered tonight was about Mike.
“Honey, Nen and I talked and she is a ladyboy and...” Mike began to say before Eileen interrupted.
“Really? I never would have guessed. Nen, you're beautiful,” Eileen blurted out before she realized Mike had more to say. Nen smiled, blushed and said, “Thank you, Eileen.”
Mike paused a moment, then continued, “So she's a ladyboy, but she isn't interested in just being with me. She wants both of us.”
“Yes, you very pretty woman, Eileen. I like both you,” Nen said in her slightly broken English. Eileen looked at Mike, then at Nen and then back at Mike again. This was supposed to be about Mike. She hadn't considered a threesome. She slept with women without Mike occasionally and had no problem with Mike doing the same, but he wasn't interested in other women. He wanted a transsexual. He loved the threesomes with other women, but if he was going to sleep with another woman alone, he wanted it to be a transsexual.
Eileen understood. She wasn't interested in sleeping with other men without Mike there. Women yes, but Mike was her man and the only one she wanted to be with alone. She guessed he felt the same way about her. She didn't want to ruin his chance at fulfilling his fantasy. She felt like she would be intruding. She almost said as much, but Mike spoke first.
“Eileen, I'd like that too. If you're OK with it, I'd like you to join us. In fact, I think I'd prefer it. I'd love to have you there my first time,” Mike said. Eileen's heart melted. It felt good to know he wanted her to share in this. She knew he was being genuine, but she needed to make sure anyway.
“Mike, you were going to do this alone. Are you sure? I feel like I would be intruding,” Eileen asked, touching Mike's arm. Mike asked if Nen would give them a minute and the girl walked a few yards away.
Mike took Eileen's hand, looked at her and said, “Eileen, you wouldn't be intruding. I thought I wanted to do this alone, but when Nen mentioned she wouldn't mind being with both of us, I thought how perfect that would be. It never occurred to me. It was my fantasy, not yours, and I just never gave it any thought. I’d love to share this with you. I'm going to do it anyway, even if you say no, but I'd like you to be there.”
Eileen smiled up at Mike and said, “OK, if you want me there, I'd love to be there too. I meant it. She's really fucking hot and I'd do her whether she has a cock or not.”
Mike kissed her and called Nen over. He explained they were both interested. They haggled with her, wanting her to spend the entire night with them. They agreed on a sum and Eileen thought it was on the low side, based on what she had read. Then Nen, leaned over, hugged her and said, “I never have a redhead girl. I like red head. You very pretty.”
Now it was Eileen's turn to blush. She guessed that explained the modest sum. Eileen had flame red, medium length, curly hair and her skin was a silky white. Her nose was lightly freckled, as was her chest just above and in between her round, bouncy breasts. Eileen was average height, but shapely with a nice round ass and wide hips. Nen was fulfilling a little fantasy of her own. Suddenly, all Eileen could think of was taking Nen's cock deep in her pussy.
“Mike, shall we?” Eileen said to her husband and then explained to Nen they were staying at a beach resort nearby. After a couple of minutes, Mike managed to hail a cab to take them to the resort. Twenty minutes later, the cab pulled into the circular drive at the resort and Mike paid the driver as the women got out. He joined them after a moment and told Eileen to take Nen down to the beach and find a cabana, while he went for drinks. Eileen asked for her favorite, a white Russian, and Nen asked for white wine.
Eileen looked at Nen and gestured for the girl to follow. This was highly erotic. She wondered what the other guests thought as they passed. Did they assume Eileen had hired a girl for the evening for her own pleasure? Did they suspect Nen was actually a transsexual? Did they wonder if the blonde Thai girl was going to fuck Eileen's brains out later? Eileen could feel herself getting wet and when Nen slipped her delicate hand into Eileen’s, she gasped.
Minutes later, they were on the white sand beach amongst cabanas and rows of lounge chairs. Though Eileen doubted they would make love to this girl on the beach, she figured a little privacy would be nice. She led Nen to the far end of the beach and into a cabana with a day bed and two wicker chairs, surrounded by thin, beige drapes hung from the dark wooden frame. The entrance faced the ocean and the nearly full moon reflecting off the water and white sand lent some romantic illumination to the interior.
The women went inside, Nen lay on the day bed, and Eileen took a seat in one of the chairs. Nen was beautiful and Eileen had to resist the urge to join her. This was about Mike she reminded herself, though she found herself wanting to make love to Nen herself. She had never been all that interested in transsexuals. Some were very pretty and she could appreciate what Mike saw in them, but she liked her men with cocks and her women with pussies, or so she thought.
Nen was so damn sexy, though. Eileen had told Mike she would love to fuck a transsexual, mainly just to get him aroused during sex, but she had never really thought about doing it for real. However, all she could think about now was straddling Nen’s small body and riding her cock until they both came. Eileen hoped Mike wanted her there for more than just moral support.
Nen reclined, propped on her elbows and looked at Eileen. Nen's short dress wasn't covering her thong well and even in the pale moonlight, Eileen could see there was a sizable bulge. She wondered how big Nen's cock was. If she had learned anything looking at transsexual porn with Mike, it was that you could never tell how big some of these girls were. She had seen tiny ladyboys with enormous cocks and six-foot tall transsexuals with little more than a few inches.
“You not like me?” Nen asked and startled Eileen from her thoughts.
Eileen's eyes moved from Nen's panties to her face, and asked, “Why do you ask that?”
“You sit there and not lay with me. Why?” Nen asked, pouting slightly.
“No, I think you're beautiful. Very sexy. I thought we should wait for Mike. He's the one that really wants to experience a girl like you,” Eileen replied.
“He very handsome. You are lucky girl,” Nen said, pausing for a moment before asking, “You don't want to have girl like me?”
Eileen, in fact, did want a girl like her. She was worried about taking over, ruining this for Mike. She was being honest with Nen. She was only waiting because of Mike. Otherwise, Eileen was sure, she would be sucking Nen's cock right about now. Eileen thought she should come clean and said, “I do want to be with you, but so does Mike. This is his fantasy and I don't want to ruin it for him. I don't want to take over. If it was just you and me, I'd already have your cock in my mouth, Nen.”
Nen smiled and asked, “We can wait, but maybe Mike like me and you to get naked for him?” The resort didn’t allow nudity. This wasn't a topless resort; much less one of those nude resorts in Jamaica Eileen longed to visit. Nevertheless, she hadn't seen a soul since they found the cabana and it seemed the other guests were more interested in the fancy restaurants and the disco than being on the beach at night. Eileen figured what the hell. Besides, it would give her a chance satisfy her curiosity about Nen's cock. Eileen hoped Nen was as big as she hoped.
“OK, good idea. Mike would like that, I think,” Eileen said and got up, kicked of her sandals, pulled her tank top over her head and then wiggled out of her khaki shorts and satin panties. Nen smiled and reached out and ran her hand over the small patch of dark red pubic hair Eileen kept trimmed just above her pussy. Eileen shivered, not expecting it, but enjoyed Nen's soft touch.
“I like your pussy very much. Very pretty,” Nen said.
Where the fuck was Mike? Eileen wanted to jump Nen so badly. How long did it fucking take to get drinks? If he didn't show up soon, Eileen was going to stop worrying about it and get started without him. Nen reached out, Eileen took Nen’s hand and knelt on the bed next to the girl. Nen wiggled out of her tiny dress revealing round breasts with cute little brown nipples that just begged to be pinched. Eileen was quickly losing her willpower.
“You like what you see, Eileen?” Nen asked.
“Oh God, yes!” Eileen replied. Nen then slipped out of her little thong, tossed it aside, and looked up at Eileen. The girl lounged on her elbows again, completely nude except for her heels, her cock lying on her tight belly.
It wasn't huge, but it was big enough. Nen's cock lay flat, swollen but not hard yet. It nearly reached to her naval. Her cock was thick and fat, its head slightly smaller than the shaft. Nen spread her legs and her balls dropped down between her thighs. She was totally bare. Eileen gasped and stared, her mouth agape, and Nen giggled and said, “You like my cock?”
Eileen couldn’t take her eyes off it. It was bigger than Mike's, but only slightly. Mike's cock was manly, covered with knotty veins and topped with a large purple head. A blonde fuzz covered his balls that he kept trimmed close, but otherwise he was shaven. Nen's cock was pretty, even feminine if that was possible. Eileen finally said, “Yes, I like your cock.”
Nen smiled. Eileen was way past waiting for Mike. She really wasn't too worried that Mike would mind Eileen indulging. She knew him well and getting upset about things like this wasn't his way. Mike usually just went with the flow. Eileen moved between Nen's legs as sat on her feet. She reached down and picked up Nen's heavy cock in her hand and Nen sighed. It was still soft and spongy, but so warm and velvety to the touch. Nen looked at Eileen, a pleasant grin on her face and then said something in her native tongue that Eileen knew meant she was enjoying being touched.
Eileen began stroking Nen's cock and massaging her balls. Nen's cock seemed to swell and harden, though it only grew slightly. Soon her cock stood erect and Eileen could feel Nen's heartbeat as she softly stroked it. Eileen’s pussy was dripping wet. She wanted this beautiful creature. She bent to take Nen into her mouth, but heard Mike as he found the cabana.